The Big Store
by CaptainMercy42
Summary: Castiel J. Flywheel, private investigator is hired to protect the up-and-coming crooner, Sam Winchester. But Sam's brother Dean already considers himself Sam's personal bodyguard. A rough start is smoothed over by the playful mute, Gabriel, and department store hi-jinx ensue. **Yes... this is ripped from the plot of a Marx Brothers Movie - because I can** (DESTIEL!) (no sabriel...)
1. Chapter 1

_**A/N: **__*singing while I sell* ...So we're all technically too young to get Marx Brothers references BUT THAT'S NOT STOPPING ME. I think you could enjoy this regardless. It's a slow start, as far as juicy love stuff goes. But it will be FUN. I'm posting now to force me to follow-through and write the rest instead of picking the beginning apart until I hate it all. As many have told you before me, reviews do indeed speed up the update process as WELL as the update quality. How amazing is that!? It's magic. _

The apartment door read "Castiel J. Flywheel, Private Eye." It looked legitimate enough. It wasn't the worst neighborhood.

Castiel J. Flywheel was a two-bit detective who graciously allowed his mute cousin, Gabriel to assist on his investigations. He could hardly pay the man, but Gabriel was dumb, not an idiot. He would occasionally do other odd jobs during their down time while skillfully ignoring Castiel's brooding silences or bouts of sarcastic self-loathing.

Castiel wasn't really a detective at heart. He had been drafted at 18 and had made a very good soldier. But by the end of the war he had grown weary of the regimented life. Once he was thrown back into normal society he tried a few regular jobs and discovered he now had a serious problem with authority. It didn't work for him unless he had it, absolutely. He decided that it was time to try out self employment.

What possessed him to become a private eye is a mystery he might never solve. Though he was more than competent scientifically he tended to come off a little stiff when meeting new people. This aloof quality was dulled slightly by Gabriel's charming innocence, but it still managed to cut many of his interrogations short.

Oh well. He was good with a firearm. He kept fit. The ladies seemed to appreciate him. That had to count for something.

He scanned the newspaper for new leads or a break on a cold case. His eyes wandered over boring headlines and landed in the funnies, where they proceeded to glaze over.

An abrupt knock brought him out of his reverie.

Gabriel stood bolt upright. He was in the middle of scrambling eggs in a cast iron pan on a hot plate atop Castiel's desk. Very professional.

"Gabriel, quick - a customer!" The words crackled out of Castiel like hail down a tin roof.

In a flash Castiel was upright and stowing the murphy bed back into the wall. Gabriel shoved the hot plate under the desk and pulled a rack of drying clothes into the back room. The office was so bare that it only took a second to tidy it up. Castiel's eyes swept the room in one last inspection.

"Apron!"

Gabriel's eyes said "oh right" as he shucked off the frilly white apron he was wearing while he scrambled their eggs. Castiel opened the door and Gabriel lunged forward to stand at his side as they greeted their mystery visitor.

A middle-aged woman in a smart suit and a respectable fir strode through the door, glancing first at Gabriel before deciding that Castiel was the man in charge.

"Mr. Flywheel? My name is Ellen Singer. You come highly recommended, and I'd like to enlist your services." She offered her hand to Castiel, gracefully.

Castiel squinted and cocked his head. His client list would have to fight dirty to beat up Gabriel's vocabulary. It was pretty safe to say that none of his business was ever based on word-of-mouth marketing.

"Who recommended me highly?" He neglected Mrs. Singer's hand.

Gabriel flashed him a quick sad-clown face, then reached out to shake the hand himself, smiling wide. Mrs. Singer pulled out of the shake rather quickly. Gabriel's face fell again.

"An old friend of the family whom you served with in Europe. Ash sends his regards."

"Ah." Castiel nodded. It made sense that Ash would throw some work his way. Ash was a kind soul who didn't really seem to be cut-out for war. He had been their communications liaison, and luckily was adept enough at interpersonal communications to befriend Castiel, which was no small feat.

Mrs. Singer looked around the barren office and her face softened.

"I'd like to hire you temporarily as bodyguard for my nephew. Have you heard of Sam Winchester?"

"No."

Gabriel shook his head, yes.

"Do you listen to the radio much?"

"Yes."

Gabriel shook his head, no.

At this point Ellen pursed her lips, and decided to direct all her energy into communicating only with Castiel.

"Well my nephew, Sam Winchester is an up and coming singer. Perhaps you've heard his newest song, _Your Face_? Regardless, he has just recently inherited the controlling shares of Winchester's Department Store. He has decided to sell his shares and use the profits to build a music conservatory for children. It's big news because of his celebrity status."

Castiel watched and listened intently and gave a slight nod. Gabriel sat himself down at the desk, opened the bottom drawer, removed a mug and saucer and poured himself a cup of coffee. Ellen continued.

"I have been told it's just my imagination, but there have been some strange accidents around the store lately and they all seem to occur around Sam. It might be nothing, but I'd like you to stick close to Sam until the sale is final and keep an eye out for any funny business. Are you available for this position?"

Gabriel pulled last year's calendar out of the top drawer and pretended to study it carefully. Castiel eyed him warily. Mrs. Singer clearly didn't have any delusions about the popularity of the detective she was hiring. She technically hadn't even asked him to do any investigating.

"I am available to start immediately."

Gabriel tossed the obsolete calendar behind his head. He tapped his foot. His expression changed, starting at puzzled and ending in pain. He looked down to see his foot in the egg pan. At that moment Castiel sniffed, and his eyes immediately darted over to the floor under his desk.

"Well that's wonderful. I can have my driver take us to the store to meet Sam right now, if you'd like."

Castiel scowled as he watched his breakfast melt onto the soul of Gabriel's boot. If Mrs. Singer had noticed the stench of burnt boot, she wasn't letting on. He nodded and gestured towards the door, allowing Mrs. Singer to pass through in front of him and lead the way to her sleek, black DeSoto.

Gabriel waved, merrily until the door clicked shut, at which time he flew off the desk chair with a silent howl, flinging his burning boot at the wall.

Winchester's was the city's premier department store, boasting seven different levels of shopping extravagance. From bassinets to fishing nets, you could find it all at Winchesters.

And that's where Sam Winchester sat now, staring out of his 12th floor office window. His aunt Ellen had phoned him that morning and asked him to meet her at the store. The request made him a little uneasy, even if it did provide him with a fantastic excuse to run into Jess from the music counter, and maybe even take her out to lunch.

"Winchester's sells everything, right? So where's the pie? Do we sell pie?"

Dean Winchester, Sam's older brother, sat hunched over on a stiff couch staring at his hands hungrily. His sandy hair had just recently grown out of its army regulation cut, and it was coiffed into a slick Clark Gable.

"Why don't you call down and order some pie to be sent up to us executives?" Sam taunted.

"Because I am not an executive. I am a mechanic in a monkey suit. Why doesn't partial-store-owner Sam call down and get them to send up some pie for his un-famous brother slash bodyguard?"

Sam narrowed every feature on his face into a series of thin lines.

"Hey, you inherited just as much as I did. I still don't understand why you signed your half away to me." Sam stood up, moodily and put his hands in his pockets.

"Because I'm fine, Sammy, and you're going places. It just makes sense. Unlike your haircut."

Sam ran his fingers through his admittedly long brown locks.

"I just can't bring myself to get it cut."

"Okay, whatever Samson."

"Would that make you Delilah?"

"You know what? Maybe I'll ask that little blonde downstairs at the music counter if she thinks you need a haircut. There's your Delilah."

Sam blushed and looked away.

Ellen Singer knocked on the door, then entered without waiting for reply. Sam and Dean watched intently as she was followed almost too closely by a nice-looking man with sparkling blue eyes, unruly hair and a tan overcoat.

"Sam, Dean, this is Castiel Flywheel. Castiel, this is Sam and Dean Winchester."

Castiel stepped forward to shake hands with Sam and Dean, politely.

"I wasn't aware there were two Winchesters." His gravely tambre gave Sam and Dean a start.

"Ah. Of course. I forgot to mention Dean. Dean fixes automobiles for a living. He signed his half of the inheritance over to Sam, and he isn't a well-known face around town."

Dean and Sam huffed and shifted as Ellen highlighted the stark differences between the two brothers.

"I'm sorry, I wasn't expecting to see you this afternoon, Dean. It's a pleasant surprise."

She smiled genuinely, and Dean returned the grin. No matter what they slung at him, he was fond of his family.

Castiel cleared his throat, knocking the party back on course.

"Sam, I have retained Mr. Flywheel here to accompany you about your business the next couple of weeks, at least until the sale goes through and the press settles down a little."

Sam's eyebrows flew sky high while Dean's face went from passive to possessive.

"Hey wait a minute, I'm Sam's bodyguard. I put a suit on and everything."

Castiel examined Dean in his suit. It was well-fitting, and disguised all traces of his work as a mechanic. So well so that Castiel imagined if Dean stood still enough in the lobby he could be mistaken for a manequin.

Ellen hardened her manor and took a step forward, abandoning a bit of her upper-class airs.

"And who's going to watch you, Dean? If someone's really after Sam you think they're going to be too stupid to realize he's got a brother hanging around to inherit it all? Please."

Dean flexed his jaw, but had no response. Sam sighed and placed his large hands on his aunt's shoulders.

"No one is after any of us, Aunt Ellen. But if you want Castiel to stick around until the end of the sale then that's fine too. Whatever makes you feel better."

Suddenly, outside the office there was a crash. A woman screamed. A shrill whistle sounded out like a bird of prey, and Castiel immediately rolled his eyes. He stepped over to the door and pulled it open wide, just in time for Gabriel to roll into the room and hop to his feet in a fighting stance.

"Gentlemen, meet my associate, Gabriel. He doesn't say much." At that moment Castiel was greatful for the fact that Mrs. Singer had already paid him his retainer fee during the car on the ride over.

Gabriel dropped his dukes and jutted his hand out to shake with Sam and Dean, happily.

Sam and Dean exchanged a look as they took turn shaking hands with the frenetic man, but neither of them were able to resist smiling back when he met their gaze with his enthusiastic grin.

"Well this has been great," Sam cut in, "but if we're all done I think I'm going to go down to the music department and check on my sales." He looked at the floor, one hand concealed guiltily in his pocket as he picked his way out of the office.

Dean rolled his eyes and huffed off after Sam.

Castiel narrowed his eyes and followed Dean.

Gabriel took Ellen's hand and kissed it gingerly, before bowing gracefully and backing out of the room.


	2. Chapter 2

_**A/N:**__ Sorry I'm sort of a short-chapter-lover. But it helps them come out quicker. Side note- google the pansy craze if you're in the mood to write some 1930's Al Capone style fics... There is TONS of fodder in those two words alone. I'm not even going to scratch the surface._

In spite of his size Sam was deceptively stealthy and managed to slide into a closing elevator, momentarily shaking his three new tails. Dean punched the down button ruefully, and they all stood quietly to wait for the next car. Well, Gabriel did pull out a harmonica, but a small head shake from Castiel got him to put it away.

A raspy, accented voice barked out from the executive offices. The trio looked over to see a short, dark-haired but balding man in a black suit strutting towards them, smoking a thin cigarette.

"Dean Winchester. You don't work here. What's the idea, bringing strays up to the executive floor? Who are these people?"

Castiel didn't appreciate the newcomer's tone, and angled himself in front of Dean, protectively. Apparently he'd taken Ellen's concern about both Winchesters to heart.

"I'm Castiel Flywheel, a purveyor of fine firs. This is my associate, Gabriel Evergreen. We were just telling Dean about our holiday collection."

Gabriel pulled a small pine branch out of his pocket and extended it towards the cranky man. It went unnoticed.

"I'm Crowley, the store manager and this mechanic in sheeps clothing has signed away his rights and is no longer a suitable chaperone for wandering vendors. If I see you on this floor again I'll have security drag you out by your neck hair."

Gabriel looked absolutely disgusted by Crowley's imagery. Dean's face was dark and scowling. But the elevator chose that moment to open, so Castiel gently pulled his comrades inside, giving Crowley a wave and an eyebrow waggle.

"Only 173 days until Christmas!" Castiel sang through the doors as they slid shut. The car fell silent. Gabriel put his tree back in his pocket.

"That guy is a giant dick." Dean sputtered.

"Dean, stop. You're making us feel inadequate. Gabriel and I are just averaged sized dicks." Castiel put his hand on Dean's shoulder, dramatically. Dean glared at Castiel for a moment, then turned to see Gabriel peering at him through an ornate magnifying glass. He began to nudge Dean in the ribs.

"Yes, I get it. Detectives. Dicks." He huffed.

Gabriel cocked his head as if the joke just dawned on him, then fell to the floor in a fit of silent laughter.

Music and housewares were on the fourth floor. Sam was sitting at the record counter staring at the very pretty blonde girl behind the counter as she sorted through records, trying desperately not to look up at him. It didn't matter. Her neck was red under his gaze and they were both guiltily enjoying the time in each other's presence, no matter how awkward.

Dean slid up next to Sam and proceeded to ruin it all.

"Hey there, girlie. All I've heard lately is Sam Winchester this and Sam Winchester that. Frankly, I'm a little tired of it. He sounds like a hack to me. I was wondering if you could recommend some real music?" He leaned over the counter and gave her a wicked grin and a wink. Masterfull. For a moment he was torn between keeping his eyes trained on Jess, or glancing over to see how steamed he was making his brother.

"I'm sorry, miss. Are these two goons bothering you?" Apparently Castiel was joining in on the fun. Dean and Sam whipped their bitch faces at him like fastballs. Jess turned, just as startled, to find a handsomely disheveled man standing directly across from her.

"Oh hello. Who might you be?" She smiled politely and Castiel returned her grin.

"I'm Castiel Flywheel, professional bodyguard."

"If you're a bodyguard, I'm a monkey's uncle." Dean muttered, feeling empty as the attention was so easily drawn away from him.

"It'd be better if you kept your family out of this." Castiel deadpanned, locking twinkling eyes with Dean before flitting them back to Jess. Sam snorted, and Dean chuckled in spite of himself.

A split second later a thunderous clap brought them all suddenly to attention. Dean's hands darted to his gun, tucked in the back of his waistband. Castiel's hand darted inside his coat. The two men noted each other's reactions with interest, while still on high alert.

But it was just Gabriel, sprawled out on the floor a few feet behind them, on top of a plywood sandwich board. He hopped up and dusted himself off, sashaying over to Castiel's side to give Jess the widest smile yet. He tugged on Castiel's arm.

"And this is my associate, Gabriel." Castiel introduced him obediently.

"Nice to meet you, Gabriel," Jess replied.

Gabriel smiled and put his elbows on the counter, resting his chin on his hands and batting his eyes like a cherub.

"He doesn't say much."

Gabriel took this moment to wolf whistle at Jess, as if that would somehow prove Castiel wrong.

"He recently lost a fight with an alley cat." Castiel offered this information as if it were the weather.

"Oh the poor baby. Did he get your tongue?" Jess cooed playfully.

Gabriel nodded, pouting. He let out a low whistle to indicate his sadness.

"Sounds more like he shoved a canary down your throat." Dean was done moping and wanted back in the game. Castiel felt something in his chest surge competitively. He turned what he hoped was his least mischievous smile back to Jess.

"Gabriel and I are currently on-duty protecting the great Sam Winchester, and I have it on good authority that he'd like to take you out to lunch this afternoon." At this point Castiel's good authority was just a hunch, but he ran with it, regardless. "I promise we won't get in your way. You'll be completely safe and unhindered."

"Is that so?" Jess asked, coyly. She glanced over at Sam with a dreamy smile, and Sam smiled back, blushing some more. If Sam kept this up much longer his heart was going to seize up from the effort of keeping so much of his blood surging to the surface of his upper body. He bravely got to his feet and walked over to offer Jess his arm. She glanced behind to make sure her replacement had come in, then stepped over and linked her petite hand behind his elbow. They walked towards the exit. Castiel and Gabriel followed them at a distance.

Castiel walked slowly, distracted by the great effort he was putting into convincing himself that he had won whatever contest of wills had just been laid out for them. He had gotten the most positive reaction from the girl (aside from Sam, but you can't count him - he already knew Jess) and he had successfully ditched the superfluous bodyguard. But something about this victory felt hollow. Gabriel eyed him thoughtfully as they trudged behind Sam and Jess.

Dean was left alone at the counter, wondering how everyone had just managed to leave him behind without so much as a goodbye. Part of him wanted to insist that he accompany Sam to lunch, but the likelihood of something bad happening at a randomly chosen restaurant was pretty slim. Add to that the fact that his new bodyguard may not be completely useless, and there was just no reason for him to tag along. He let out long sigh.

Suddenly there was a tap on his shoulder. He turned to find Gabriel standing beside him, holding a card that simply read "invitation." He plucked it out of Gabriel's hand, delicately.

"To lunch?"

Gabriel nodded.

"Castiel won't mind?"

Gabriel fought to suppress a smirk as he shook his head, no. Dean looked around the store, looking for an excuse to lean one way or the other. Nothing came to him before his eyes fell back on Gabriel's earnest expression.

"Aw, what the hell."

Once the three of them were installed successfully at a table within full view of Sam, Jess and all the exits, their lunch proceeded rather normally. They had cheeseburgers and Cokes all around, with Dean and Castiel chatting idly as they waited for the food to be served. After they were finished wolfing down their burgers, they realized that Sam and Jess were only just starting to eat. Castiel ordered Gabriel a milkshake to buy them some more time at the table.

"So do you guys live together?" Dean asked, trying to sound nonchalant.

Castiel looked at him, then cocked his head and narrowed his eyes. Finally he smiled ever so slightly.

"Gabriel and I are cousins. And no, we don't live together. He cares for his mother in the evenings, and I live in my office."

Dean nodded, crunching on a pickle, thoughtfully.

"What about you? Is there a Mrs. Dean Winchester at home?"

Dean shook his head.

"I've got a little apartment above my garage. Not a lot of room for a family. Sam stayed with me for a while, but there wasn't really enough space for both of us, so he got his own place once his music checks started becoming regular." There was a twinge of regret in Dean's voice, but he didn't think either of them would notice. He glanced over at Sam and Jess who were nibbling their way through a slice of apple pie one infuriating little bite at a time. Castiel's eyes followed his.

"How would you like to handle the night shift? I assume that you were planning on keeping an eye on Sam outside of normal work hours."

Dean's head snapped back around to their table.

"Isn't that what you're getting paid for?" Dean grumbled.

"Well I'd be honored if you felt comfortable enough to leave it in our capable hands." Castiel countered.

Gabriel slurped the end of his milkshake, noisily.

Midnight found the motley crew of investigators piled into Dean's parked Chevrolet in front of Sam's new cottage. Gabriel snored quietly in the back seat, curled up like a child, his head on a pillow, his hands clutching a soft blanket under his chin. Dean and Castiel sat stiffly in the front, shelling peanuts to pass the time, occasionally taking swigs out of a flask that at one point they had begun sharing. Castiel was squinting, as usual.

"Spit it out, Cas."

Castiel looked over at Dean, questioningly.

"A nickname?" His voice was especially low in an effort not to wake Gabriel. Dean ignored his question.

"I know you've got questions about Sam. About this-" Dean waved his hand towards Sam's cottage. "Let me have 'em."

"Well, no one has given me a specific description of exactly who might be trying to hurt Sam, and why. I feel unprepared for the assignment of his protection, and confused as to how thorough I should be."

Dean sighed. Castiel was a stranger, but he wouldn't be very useful to them if left completely in the dark.

"Well, look. Here's how it is. Sam and I grew up with a drunk for a dad and no mom to speak of. We ended up doing a lot of odd jobs for the North Side Gang, and that's who discovered Sammy could sing. One of the head honchos took pity on us, or something, and got Sammy a bunch of music lessons and training. My dad complained but they gave him free booze and he shut up. I didn't really know what to think. He was off the street hanging out with cultured folks. I figured it could be worse."

Castiel nodded, his mind flitting back to the headlines he had just read about the war between the North Siders and Al Capone's gang.

"So now we're grown. Dad's dead. We've got real jobs and Sam's a legitimate act. There's a lot of publicity about the music and the store. It's all coming together." Dean's voice trailed off as he gazed at the dark exterior of Sam's quaint little house.

"You're waiting for the other shoe to drop."

Dean chuckled. "You could say that again."

"That would be redundant."

Dean shook his head and exhaled with a smile. He reached over and patted Castiel's shoulder. He let his hand linger a moment, feeling the solid muscle hiding under the baggy suit and trench coat.

"You know what, Cas? You're alright. I mean, we're going to have to come up with a better way to keep an eye on Sam, because I'm not spending another night in my car with you and Gabriel. But you're okay in my book."

Castiel gave him a little smile. Gabriel snorted at the sound of his name, and scratched his nose.


	3. Chapter 3

**A/N: **_Managed to get another character in there. It's tough sometimes. Hate to be lame, but the chapter AFTER this is 90% likely to have more people/action. Ah well. Thanks for reading._

The three men had effectively abandoned their vigil around 5 AM, when a spastic kick on the back of his seat awoke Dean and he found that they had all passed out and left the guarding of Sam to the angels. He felt a surge of guilt as his eyes darted around the neighborhood. Everything seemed to be in order. It was just before sunrise, but looked more like twilight, the street lamps glowing orange through the otherwise bluish haze. Dean's sleep-addled mind wandered around trying to remember what exactly the color of the horizon was reminding him of. His eyes settled on Castiel's eyelids, and they opened with a start as if they could feel his gaze. Dean almost jumped, realizing that he had two drops of sunrise staring him down from only a couple feet away.

"Hello, Dean."

"Sleeping on the job?" He tried to look stern.

"Gabriel relieved me." He answered, defensively.

A little whistle from behind them made gave them both a start. Gabriel was sitting up straight, his eyes bright, with no pillow or blanket to be seen, which baffled Dean who had checked only moments earlier to find his eyes twitching under their lids. Gabriel's eyes were now trained on something, and he reached forward and grabbed their shoulders. They followed his gaze to see a long black Mercedes creeping down the road in front of Sam's house. They all three instinctively ducked as the car crawled past them, headlights suspiciously unlit.

Dean whipped around in his seat to watch as the car trundled away, trying to get a glimpse of the the two hatted figures in the front seat. It was a fruitless endeavor, and he sat back with a huff.

"Well that was odd." Castiel offered, in a gravely morning tone.

Sam awoke with a start as he heard his front door open quietly, then click shut.

"Dean?"

"Yeah, Sammy. It's me."

Sam sighed with relief, then stiffened again.

"What's wrong? What time is it? Are you alone?"

Dean inched into Sam's bedroom and smiled at the fact that his sasquatch of a brother was destined for a lifetime of ill-fitting pajamas.

"Yeah we kind of staked you out last night. I just sent Cas and Gabe home to get cleaned up. They're gonna meet us at the store at 9:00 AM. You have meetings all day, right?"

Sam rubbed his face in confusion.

"Don't they live on the other side of town?"

Dean jaw twitched and his eyes darted to the window.

"I sent them home with the Chevy."

Sam's jaw hit the floor.

"You let Castiel drive your car?"

"Yeah. Did we need it? Is something wrong with yours?"

"Um no. Something's wrong with my brother. You're letting a guy you just met drive around in your most prized possession without you. You do realize that you've actually told me not to _look_ at your car before, right? And now there's some stranger in there molesting _her_ and you're okay with that?"

"The man was in a war, for God's sake! He knows how to drive." Dean responded, choppily. "And you're my wealthy, successful little brother! I don't have much to lord over you. If I have to use my car, so be it."

Sam chuckled and shook his head. He swung his legs over the side of the bed, his long locks tickling his eyes. He stood and stretched and embarked on his morning routine, brushing his teeth and slicking his hair back carefully with a fancy pomade. He could hear Dean pacing around the house aimlessly, examining the trinkets and photos that Sam had collected now that he was on his own. Sam heard him sigh.

Finally he emerged, freshly suited and ready for a day of grueling shareholder meetings that he had absolutely no interest in, but was unfortunately competent enough to attend. After that he was going to be introduced to the men who were going to potentially buy his shares in the store. His chest knotted a little bit as he thought of the great things he was going to do once he was out of the department store business forever.

Dean was examining a postcard from Kansas when he noticed Sam standing in the doorway, ready to leave. He set the card down and gave him a grin.

"Ready to shake a leg, Samson?"

Sam rolled his eyes. Dean held him back when they reached the door together.

"Bodyguard first," Dean insisted, and led the way, scanning the street for the black Mercedes or anything else that might seem out of place. Sam locked the door and they walked over to his car.

"And Sam?"

"Yes, Dean?"

"When I get my baby back later today, if you so much as look at her funny, I will fight you."

Cas and Gabe miraculously arrived at Winchester's before Sam and Dean. The store hadn't opened yet, so they loitered outside, watching businessmen clutch their briefcases and rush to their prospective offices. Gabriel made sure to eye each one as if they were a potential threat, though they all looked nearly identical in their grey or tan overcoats and fedoras. Consequently, Gabriel was doing quite a lot of suspicious squinting.

"It's a pity the criminals don't dress in a manner different from the general populace that would make them easier to identify." Castiel stated.

Gabriel turned and gave him an earnest nod. Castiel just chuckled and chewed on a toothpick, absently.

"Hey, you two! What's the big idea?" The gruff voice of Crowley pierced through the hum of the crowd. He cut through the sidewalk traffic, and stomped up to the detectives.

"Hello, again Mr. Crowley. What a pleasant surprise. Just so you know, we're first in line for the big humidor sale. You'll have to get behind us." Castiel spoke evenly and gave Crowley a small smirk.

Crowley fumed, pulling his hat off to reveal that his head was literally hot with rage.

"Now you listen to me! I don't know what you're on about, but I'll not have you loitering in front of my store like beggars."

Gabriel dropped a dollar into Crowley's upside-down-hat, then pointed at Crowley accusingly. Crowley tipped his hat over and dumped the dollar out in disgust. He lunged towards Gabriel, but Gabriel had already zipped behind Castiel, who stood his ground calmly. This flustered Crowley, who hadn't been exactly sure what he was going to do once he got his hands on the nimble mute.

"Have we met?" Castiel reached out his hand and plastered a fake smile on his face. "I'm Castiel Bourbon, a seller of fine liquor. Or you could lick him with no ballyhoo from us. I'm utterly indifferent." Castiel shook Crowley's hand as Crowley shook with rage.

Gabriel pulled a pansy from his pocket and danced by Crowley, stringing the flower behind his ear.

Sam and Dean pulled to the curb with a rumble and immediately noticed Crowley looking a bit like he was going to explode. There was inexplicably a flower behind his ear and a dollar at his feet.

"Is everything alright here, Mr. Crowley?" Sam asked cautiously, knowing his brother hated the man and wouldn't initiate contact unless forced.

Crowley flicked the flower out of his hair and turned to Sam sharply.

"Fine, Mr. Winchester. I was just getting ready to call security." His demeanor morphed into the sickly smooth calm of a manipulative bastard.

"Call security on who?" Asked Sam, genuinely.

"On these charming fellows right here." Crowley nodded his head towards Castiel and Gabriel.

"But sir, these are my bodyguards. That's Detective Flywheel and his assistant Gabriel.

Dean grimaced. He hadn't wanted anyone to let on to Crowley that they were watching Sam. He just didn't feel like he could trust the guy. Castiel had seemed to understand this implicitly, but now Sammy had gone and blown their cover.

"Bodyguards? I see."

No one liked the croak in Crowley's voice, or the way his eyes darted and weaved along the ground in a calculating manner.

"Well then. Perhaps it was all misunderstanding." He turned back to face Cas and Gabe. "I apologize for the miscommunication. You are welcomed to the store when Sam is on the premises." Crowley turned on his heel and entered the building without giving anyone time for a response.

"Well that felt weird." Dean and Cas exchanged an ominous glance that they were planning to share with Sam until he was distracted by Jess approaching the store to punch-in for her morning shift.

When Sam made it to the executive offices he was immediately woman-handled into the boardroom by his temporary, but efficient secretary, Becky. Castiel and Dean followed, reluctantly until Becky whipped around and addressed them in a shrill voice.

"I'm sorry, where do you think you're going?" She was slight, and her long hair was knotted fashionably at the top of her head.

"I'm Castiel Flywheel, Sam's bodyguard." Castiel stood awkwardly for a moment, waiting to see if Becky would offer her hand for shaking. He cocked his head as he watched a flood of joy and relief flood her face and change her expression from completely collected to certifiably crazy in the course of one short second.

"Oh that's wonderful! I like to keep an eye on him, but I can't be everywhere. And ever since he got the plans for the conservatory he's been meeting with all manner of people and it's difficult to vet every single one of them, though I've cleared most everyone he's met with one-on-one. But with his performance at Chez Paree coming up I've been even busier because all those night-club people end up looking so seedy and every man could have a gun stashed pretty much anywhere, whereas I have to keep mine in my purse but then again the night club people just seem to like music and -."

Castiel reached out and grasped Becky's shoulders as gently as possible in an attempt to somehow slow the rate at which she was delivering information. Dean stepped in closer, entranced by the seemingly innocuous secretary and her vast knowledge of Sam.

"You've been watching Sam?" Dean asked.

"Uh. Well. I mean. I've been keeping an eye on him. Someone has to. He's going to be super famous, you know!" Becky looked from Dean to Cas, her eyes questioning whether they understood how imperative her mission was.

"And you have a gun in your purse?" Castiel narrowed his eyes at her, not letting that little detail slip by.

Gabriel popped up beside them with her purse, twirling a little two-shot pistol around his finger. He whistled a greeting.

"My gun!" Becky screeched. Castiel pulled her forward while Dean tried to cover her scream. The three of them were now nestled together in a startled knot.

"Shhhhh!" Dean chided.

Gabriel put the gun in the purse and placed it on Becky's desk with a guilty look. He backed up into a plush armchair and curled his knees up under his chin. Meanwhile the Becky sandwich had yet to move.

"Okay." Dean cleared his throat. "On the count of three we're all going to let go. Becky is not going to scream, and Gabriel isn't going to touch anything else that doesn't belong to him."

Gabriel put his hat over his face in shame. Dean counted to three and released Becky's mouth, wiping his noticeably moist hand on his pants. Castiel extended Becky an arm's length away then finally lifted his hands gingerly from her shoulders. Gabriel slid out of his chair, slunk up to her and returned her purse, which she gripped tightly.

Dean chewed his lip. Castiel gave Becky an appraising look. Gabriel gave her a daffodil, which seemed to win her over.

"Okay, Becky. We're going to leave you in charge of guarding Sam when he's in these offices."

Becky's eyes glowed and she looked like she might suddenly float away. Castiel grimaced momentarily, but seemed to resign himself to the idea. He stepped forward to speak in a lower tone.

"You also have to keep an eye on Crowley. I don't trust him."

"Sheesh. You don't have to tell me twice. That guy's a slimeball, and all the worst looking characters are always coming to see him."

Cas checked Dean with a glance that seemed to ask if leaving Sam alone with only a Becky to fend for him against Crowley was a wise plan. Dean mouth-twitched back a solemn grin which seemed to remind Cas that there were a lot of other people in the offices, and it was an unlikely place for a showdown. Cas nodded. Gabriel rolled his eyes and crossed his arms over his chest, looking very dramatically neglected.

"Wow. You guys make a great pair- uh- team." Becky couldn't translate the eye conversation that had just flown by her, but that didn't mean it didn't completely turn her on. Gabriel huffed. "Threesome," Becky spouted apologetically. "A great threesome." She laughed, nervously.

Dean shook his head and brushed his hands on his suit. Cas watched him out of the corner of his eye.

"Alright, boys. Let's go. If you need us, we'll be in the bed department."

He ushered Castiel and Gabriel out of the executive lobby and back over to the elevators.

"The bed department?" Castiel asked, quizzically.

Dean and Gabriel turned and gave him identical looks of disdain.

"What, you're not tired?"


	4. Chapter 4

_**A/N: **__Another 2,000 words... It's like I have an internal word limit. Sorry if this feels slow. I'm always so impressed by people who can two possibly straight guys feeling each other up in 3 chapters. You people have a gift. I suppose I'm still in training, though in my defense, the 1930's are an unfamiliar angle of attack._

Winchester's was an opulent store. In the beginning Sam had questioned how they made any money at all with their elaborate product displays and seemingly endless supply of salespeople. Now he was stuck hearing about the store's fiscal success for the better part of the day, only interrupted ever so often by his odd assistant, Becky, cracking the door open to peer at him appraisingly. After the third peek he rolled his eyes, convinced that her watchful eye likely had something to do with Dean. He'd been working with Becky for a little while now, and he knew she didn't need any encouragement.

Dean, Cas and Gabriel immediately took the elevators to the first floor and made their way straight to the bed department. It was a wide area of the store that featured beds of all shapes and sizes, from grand mahogany king beds to the poorly-disguised murphy bed in Castiel's office.

Lucky for them there was only one salesman scheduled to cover the whole department. Unfortunately he was a bit bored, and greeted them as soon as they stepped into his territory.

"Mr. Winchester. Good morning." He looked down his nose at Dean and his two companions.

"Zachariah." Dean groaned, internally. Zachariah was a tall, balding blowhard in a heavy grey suit. He stood at attention behind a high cash register which was situated so that he could have a full view of the entire bed department. Dean sucked on his cheek for a moment.

"Zachariah, I'm surprised to see you here." Cas pushed past Dean with a jaunty air.

"I'm sorry, do I know you?" Zachariah looked down his nose at Castiel, his weasely little eyes only slightly betraying his utter confusion.

"You haven't had the pleasure, but I know you." Cas's voice was so low it was almost ominous. "You're Zachariah. The boss has been screaming about you all day. Why, he called you six or seven times while I was in his office!"

Dean watched with fascination as Cas let himself become more animated, fueling his ruse with enthusiasm.

"That's impossible," Zachariah droned. "My phone hasn't rung once this morning."

"No sir, you are impossible. I watched him dial, 5-6-4-3-7."

"That's ridiculous. The number down here is 4-2-7-9-3. He wasn't even close." Zachariah was a king of condescension.

"So it's 4-2-7-9-3 you say?" Cas repeated. He turned and looked at Dean. Zachariah sighed with annoyance and leaned over to read the card taped to his telephone unit.

"Yes. 4-2-7-9-3. It's written right there."

Gabriel kicked Dean. Dean shot him a look of annoyance, and Gabriel caught his eye and quickly pointed out an in-house telephone mounted on the wall across the the store. Dean gave a sigh and turned back to Cas and Zachariah.

"If you'll excuse me, I have to use the little boys room."

Dean was rewarded with an amused smirk from Cas. Zachariah had begun picking lint from his jacket as if they had all left, and didn't look up. Gabriel had taken up dusting the countertop with the small broom he kept in his pocket.

There was a lull as Castiel looked over the bed department, deciding which model he'd be testing. He settled on a large, dark wood model with a fluffy white comforter. Zachariah finished picking at his clothing and eyed Castiel suspiciously.

"Why are you still here?"

"Well it's true, I've had my share of close-calls. At this point that's a question only God can answer, though I doubt he ever will. That would undermine the importance of faith, and a religion that has no need for faith is just science, really."

Zachariah sneered at Castiel and began to look pointedly peeved. He was interrupted by a middle-aged couple wandering into the bed department. But before he could move from behind his counter to greet them, Castiel had already stepped forward.

"Good morning, sir and madame. May I help you?" He clasped his hands behind his trenchcoat and gave the couple a winning smile. The man was 10 or so years older than the woman, hiding his bald head under a bowler while she clutched his arm possessively and gazed out from behind her netted hat.

"Hey what's the big idea? You can't help them!"

Castiel didn't look away from the couple.

"You'll have to excuse this man. We caught him impersonating a store employee earlier and we're making him work as punishment."

The customers looked confused, and they made little utterances of surprise, like tittering birds. Zachariah huffed over and addressed the couple, who flinched slightly as he approached. Gabriel trudged in step behind Zachariah, mimicking his every move and mouthing his words.

"I'm so terribly sorry. It is actually this man here who is impersonating an employee. I'd be happy to show you the department if you just follow -"

The phone behind his desk rang noisily.

"You're busy. I'll get it. It's probably the brass." Sang Castiel in his raspy baritone. He ran over and grabbed the phone behind the counter, turning his body and talking into the wall for privacy.

"Hello, Dean."

Dean's chuckled over the phone line. _Hey, Cas. You miss me? _Now it was Castiel's turn to chuckle.

Gabriel was still mimicking Zachariah with surprising accuracy. Zachariah was gesturing around the bed section, but when he noticed his customers shooting furtive glances behind him, he whipped around to see what was going on behind him. Gabriel immediately dropped the act and threw his hands in his pocket, leaned on the counter and began to whistle innocently. He resumed the mimicry when Zachariah turned back around.

"Can you keep it down over there? I'm having trouble hearing Mr. Crowley." Castiel turned back to the phone and began talking loudly. "What's that, sir? You'd like to see Zachariah upstairs? Yes, sir I told him that...well you know how he is... Well sir I don't think you have to go that far... Okay I'll tell him, but I don't think you'll appreciate me using that kind of language in front of customers..."

Castiel turned his head away from the phone receiver and shouted.

"Crowley says to get your big monkey butt upstairs. His words, not mine."

Zachariah turned red with rage. His hands began fisting the air at his sides. Gabriel had to hold his breath, puff his cheeks and cross his eyes in order to reach the deep shade of magenta that Zachariah had blossoming up his neck. This seemed to be the last straw for the skittish couple. The husband sputtered a bit, incoherently and then pulled his wife away into another part of the store. Zachariah stormed off after them, making his way to the elevators. Gabriel waved goodbye. Cas smiled and turned back to the receiver.

"Dean, why don't you call Becky and have her keep Zachariah in the office waiting room until around, oh, half-past one?"

_Can do. Later, Toots. _ And with that, Dean and Cas hung up.

The rest of nap time went by without incident, until Sam arrived to shake them all awake.

Castiel sat up with a start and a look of sheer annoyance. He ended up kicking Gabe and grabbing Dean's forearm in one swift motion. The other two men snorted with the violence of their righting.

"Gee, guys. A whole department of beds and you all pick this one." Sam looks mildly concerned for a moment, before giving in to innocent sarcasm.

"It's the only one not in view of the register." Dean grumbled.

"It's settled. I'm putting it on our registry. The cat simply adores it." Cas reached forward and patted Gabriel's tousled locks affectionately, and the man stretched like a feline in return.

"Whatever you say, sweetie." Dean had swung his legs over the side of the bed and was palming one of his eyes. Eventually he'd have to take a moment to sit and ponder how he and Cas had fallen into this odd domestic banter. Eventually.

Sam's eyebrows furrowed for a minute, then sprung back to his standard young and carefree position.

"We got invited to Bobby's for dinner. The whole gang. I was just going to go to the fourth floor and invite Jess, if she hasn't already got plans." The towering man began to look apprehensive. But Dean was still smacking himself lightly in the face.

"I'm on it. To the fourth." Cas reached over to pat Dean on the knee, then swung out of bed to lead Sam upstairs.

Gabriel miraculously produced a hot pot of coffee from deep within his billowy coat. He poured Dean and himself a cup, using a display model bed table to hold their saucers. Dean sipped his contemplatively.

Sam and Cas entered the elevator alone and rode in comfortable silence. It stops on the second floor and two men in trench coats joined them. They were stocky fellows with faces that looked like chewed bubble gum stretched lumpily over pitbull snouts. Sam's head was in the clouds as he prepared to invite Jess out for a night on the town, but Cas couldn't help notice how the men's eyes widened with surprise as they looked up at Sam, then shared a suspicious glance between themselves. Cas crossed his arms to have his hand closer to his firearm.

One of the men reached towards the elevator buttons to choose their floor. Suddenly the car went black. Sam blinked with surprise, then grunted as something hard crashed down on his head. Cas reached forward, attempting to throttle anyone in an overcoat. He made contact, and flung one man onto the floor, surprising the guy with his aptitude for pummeling ugly faces in the dark. The elevator doors finally opened on the fourth floor, and the second attacker bolted through them while Cas used the growing seam of light to check on Sam. Sam had taken a decent blow to the forehead, and a tiny trickle of blood snaked between his eyes and down the side of his nose. Cas propped him up and patted his face until he came to.

"Sam. Sam, wake up."

The other attacker groaned. Cas quickly flipped the man onto his stomach and sat on his back. A young woman tried to board the elevator, then screamed. Finally. Store officials were alerted. An alarm was sounded. Gabriel and Dean appeared within minutes, out of breath from a run up the stairs. They had been alerted on the house phone by Becky, who had also come down to stand outside the fourth floor elevator and wring her hands with nervous anxiety.

Dean waved his hand in front of a woozy Sam while Castiel handcuffed the captured attacker with some cuffs borrowed from a floorwalker.

"Hey there, big guy. How you feel?" Dean smiled, nearly concealing the furious concern that was eating away in his chest.

"Dean? What happened?"

"You were knocked silly, probably by this guy Cas is sitting on."

Sam sat up and was greeted with a smattering of shy applause. He blushed, and gave a little wave, which made dean guffaw.

"Geez. If this is how they react to you waking up, I'd hate to see what they do when you sing."

"Shut up, jerk." Sam winced and touched his head, gingerly.

"I'm very sorry, Sam. I'm afraid I didn't guard your body very effectively."

"It's okay, Cas." Dean interjected, reaching over and patting Cas's arm. "You got one of them. Looks like you really did a number on him." The lunk of a man's face smushed into the worn elevator carpet.

"Yes and no. He was also pretty hideous before I decked him."

The store medic pulled Sam into an employee lounge and patched up his head. Dan, Cas and Gabriel huddled by the lounge door, speaking with one of the police officers who had been summoned to collect thug #2. For all intents and purposes, his name was Jimmy the Boot, and he'd done a lot of work for Al Capone's gang, though he didn't seem to be exclusive.

Cas grit his teeth as Dean pinched the bridge of his nose. Now it was real. Someone really was out to hurt Sammy. Someone with possible ties to one of the cities most notorious gangs, who was generally up-in-arms about regarding the end of prohibition.

The medic began packing his scissors and tape, and Sam shook out his hands.

"Hey, guys. We've still got dinner at Bobby's, right? I haven't gotten a chance to ask Jess if she can come."

They were just bidding the cop farewell, and Dean smiled at Sam, in spite of himself. He pulled the lounge door open to reveal Jess waiting just outside with a sweet, concerned expression. Becky lingered not far behind, glaring at Jess with the venom of a thousand mediocre brunettes. Both girls drank up Sam's relieved grin like it was about to become an illegal substance.


	5. Chapter 5

**A/N: _So I love you all and I love writing this and I love torturing everyone with short chapters and I love all of this. Pretend I'm drunk and find that endearing._**

...

Bobby Singer had inherited the majestic Singer Hotel from his great grandfather, the oil baron. It was a 25 story jewel in the thick of the city. Ellen Singer was in charge of the Roadhouse, the hotel's main restaurant. The lobby was a shiny, angular space with lots of glittering marble and brass inlay. The restaurant was one of those fancy jobs, with a slightly raised stage in one corner for classy dinner entertainment. Across from the stage, through the sea of crisp white tables, was a long and inviting bar that left plenty of room for the customers who weren't necessarily looking for dinner. In the center of the room the tables parted for a dance floor.

They had phoned ahead to let Bobby and Ellen know what had happened at the store, and Bobby suggested that they all stay in a suite in the hotel that night for safety's sake. Everyone agreed that spending a little time outside of their usual habits would be prudent. They took quick trips to each of their houses, packing up suitcases of dinner clothes and pajamas, then drove around the city a little more to make sure they weren't being followed before finally pulling up to the Singer Hotel.

"Swanky." Cas observed as he gazed up at the imposing building. Gabriel nodded, his eyes following the same path. Dean's eyes followed theirs as he allowed himself to look at the familiar landmark with fresh eyes, until he finally felt the heat of Cas' gaze on himself. He caught Cas squinting at him, a look that was fast becoming familiar. He replied with a self conscious, tight-lipped grin, then started off for the door.

"Don't rush in on my account. I can stand here all day." Sarcasm oozed out of the gangliest bellboy in Chicago. His suit was red and pressed to perfection, but his hat sat atop his head, jauntily out of place. He offered a wide grin to the party that was full of genuine warmth and welcome.

"Hiya, Garth." Sam smiled strolled through the door. Cas and Gabriel followed, tipping their heads politely. Dean brought up the rear and paused to shake Garth's hand. Garth grinned even wider and pulled Dean into a friendly hug, clapping him on the back like an old friend.

"Oomf. Take it easy, Garth. I've got a reputation to uphold." Dean grunted, but clapped Garth on the back just as hard.

"Bah," Garth guffawed. "Reputation? Nobody's ever heard of Dean Winchester." His eyes danced mischievously. Cas heard the exchange clearly, but couldn't extrapolate a context where the words made much sense. The detective within him catalogued the comments for further investigation. He glanced at Sam for possible insight, balking slightly when Sam knowingly met his gaze with a look that said _I'll tell you later. _It was then that Cas realized he seemed to be investigating the wrong Winchester brother. He chalked it up to idle curiosity.

Ellen Singer greeted them warmly and escorted them to a table big enough for ten. Jess had been waiting for Sam in the lobby, and Ellen promised to return shortly with Bobby in tow, though he wasn't too fond of eating in the restaurant. Cas eyed the additional empty seats and wondered who else might drop in on their meal.

He didn't have long to guess before a high pitched squeal revealed their first dinner crasher.

"I'm not late, am I?" Becky flounced into the seat across from Sam and gave him a bubbly grin which fluidly morphed into a rather put-out scowl as her gaze shifted to Jess. She had placed herself in a chair between Dean and Cas, and they were both glaring at her with a bit of trepidation. Dean cleared his throat and gave Cas a pointed _she was not invited to this _glare. Cas replied with a _there's no way to tell her that now _shrug. Sam and Jess looked a bit confused. Gabriel tucked the tablecloth into his collar like a bib and began buttering a roll.

"We could use an interpreter for these two, am I right?" Becky wagged her thumbs at Dean and Cas, still as tuned-in as ever to their wordless chatter.

Dean coughed abruptly and dropped his head for a moment, meeting Sam's questioning scrutiny when he looked up. _What's this about wordless conversations with Castiel? _Sam squinted at Dean. Dean sent a terse _she's here isn't she? That's where talking in front of her will get you _dip of the head back at his brother. Becky fanned herself with her napkin, eyes plastered on Sam. If Jess noticed she did a fine job keeping her face dreamily serene.

"Well look what my mom dragged in." Another female voice pierced through their silent conversations as a curvy blonde dumped herself into the seat next to Sam. Her dress was a little on the casual side for dinner at the Roadhouse, but that was the prerogative of the bosses' daughter.

"Hello, I'm Jo Singer." She offered a casual wave to Jess, Becky, Cas and Gabriel before launching into a rather artful interrogation of her new dinner companions. Castiel took notes.

"So you must be Castiel." She started. "I've heard about you." She left that remark hanging in the air while she turned to Jess. "And you must be Jess. I'm the boys' cousin. I've heard so much about you. He practically gushes." She grinned gaily at Sam's obvious embarrassment. Becky scowled. Jo ignored Becky completely. "Hey Dean-er, long time no see. Who's this guy?" She jutted her nose towards Gabriel. Before Dean could think of the easiest reply Gabriel slid a note across the table to Joe. She eyed it, warily before picking it up and unfolding it.

"My name is Gabriel. I call him Deano sometimes." Jo read the note out loud. Dean chortled. Jo let the first hint of uncertainty slip through her confident shell as she examined Gabriel thoroughly. He batted his eyes at her, resting his chin on the backs of his interlaced fingers.

Bobby and Ellen joined them then, which effectively ended the wandering conversation. The group made polite small talk throughout the meal, then dispersed to dance after dessert. Gabriel grabbed Jo up before she could protest. Her family watched tensely, waiting for some kind of explosion, but as it turned out, Gabriel was a fine dancer and was behaving (overall) like a gentleman.

Sam pulled Jess to the dance floor, a bit sheepishly. When Dean turned to invite Cas to forgo dancing and monitor Sam from the bar, he found himself face to face with a very expectant Becky. _Real nice, Cas. _He grumbled internally, wondering if Cas could hear him gripe without the benefit of eye contact.

Dean wasn't sure exactly how he had gotten saddled with Becky while Castiel pranced around the room with a glamourous stranger. Cas' girl had long red hair that looked like lava hanging over her emerald green gown. She was willowy and graceful and was probably not stepping all over Cas' feet while craning her neck to stare at Sam and Jess as they executed a blissful foxtrot. Dean's toes began to ache with jealousy.

One song ended, but another started up just as quickly, and Becky's grip was like iron. Dean spotted red hair and green sparkles, and his eyes jumped up to meet Cas's. They only had a moment before being whirled apart, and they each took advantage.

_Dean, can I help you? _Cas's blue eyes twinkled a bit too merrily as he cocked his head to the side in time with the music.

_For the love of God, Cas. Get. Me. Out. Of. This._ His green gaze shot back, angrily.

The moment ended, and Dean was twirled to a new angle where he caught glimpse of Gabriel and Jo high-stepping across the floor. The two seemed to be revelling in their outlandish dance moves, easily ignoring the sideways looks from the older patrons. Dean smiled. He liked to see people having fun. Becky promptly stomped the smile off his face with her right heel.

"Excuse me, may I cut in?" Cas stood stone-still beside them, in stark contrast to the sea of dancing couples. It was like he had materialized out of thin air. Dean coughed with surprise, and Becky made a sound like a hiccup.

"Oh. I suppose so." She released Dean from her clutches and turned towards Cas, but he already had Dean by the elbow, leading him towards the bar. Becky's face twitched in shock. Dean looked away purposefully, but Cas couldn't follow-through with his abandonment. He paused, then leaned in to speak lowly into her ear. Whatever it was, it sent her eyebrows back up to standard crazy-Becky height, and sent her scurrying out of the restaurant.

"What'd you tell her?" Dean sidled up to the bar, finally, and ran a hand lovingly over the smooth marble countertop, his eyes searching the floor to check up on Sam.

"I, uh..." Cas looked conflicted. "I told her that the bellboy Garth had looked very suspicious, and that I thought I'd seen him watching Sam. I believe the two of them might... hit it off."

"What are you, Cas? A bodyguard, a detective or a matchmaker?" Dean feigned suspicion. His silent laughter brought Cas's gaze back from the dance floor, where he had also been searching for and confirming Sam's presence and safety.

"All three." Cas swung his eyes back around to Dean. "And not a bad dancer, either."

"I'll have to take your word for it."

"For now."

Dean furrowed his brow for a moment, then scanned the bar, his eyes travelling over a few exceedingly handsome couples. He watched a bit forlornly as the women puffed on long cigarettes, leaning towards their sharply-dressed dates suggestively, occasionally fondling a lapel or pushing the men away with an overly playful laugh. He caught the bartender's eye and ordered two Old Fashions.

"You got any introductions for me, Cas?" Dean asked, eyes focused on the drinks as he slid one to his new friend.

"No."

"Hey now. I'm giving you plenty to work with, here." Dean asserted, with as much humility as can be mustered while simultaneously gesturing towards oneself in a way that suggests one is the total package.

Cas took a thoughtful sip of his drink, and squinted at the dance floor, chewing the corner of his mouth. He turned back to Dean.

"Because I think it will be a cold day in Hell when Dean Winchester finally meets his match." The twinkle in his eyes was slightly dulled by a flash of what may have been conviction. Dean's subconscious put a mental bookmark into this statement, and promised to return later with his conscious mind in tow for further examination.

"My matchmaking skills have always been most beneficial to people from whose company I wish to extricate myself. So you're out of luck."

They sat for a couple minutes in an effortless silence. Dean drained his glass and stood up.

"I'm going to dance my way over to Sammy and see if he's almost ready to call it a night."

Cas nodded, and Dean set off towards the side wall where the same glimmering redhead from earlier was enjoying a cigarette by herself. He gave her a winning smile and offered her his arm. She accepted, and they hit the floor with grace. Dean was a talented dancer when he wasn't saddled with a Becky. Cas watched as he led his former dance partner effortlessly across the floor while holding whispered conversation that seemed to amuse the redhead greatly. Cas wondered what they were talking about. He hadn't exchanged more than a few necessary pleasantries with her, himself.

Dean finally had danced them to the far corner of the room where he gave Sam a brotherly pat on the shoulder without missing a step. At the end of the song both couples left the floor. Dean politely extricated himself from the redhead and snagged Gabriel and Jo to convene with everyone else at the bar. Jo reached over a grabbed a bottle of gin off the top shelf, unwavering under Dean's questioning gaze.

"For the room. You didn't think you were getting rid of me that easy, did you?"

"It's never been easy to get rid of you, Jo. At least you're contributing this time." Dean laughed.

"Hey! Don't get mad at me! Gabriel invited me."

Gabriel grinned from ear to ear, his eyes widening while his eyebrows remained in their proper place. It was almost creepy. But it wasn't quite as creepy as the awkward goodbye going on between Sam and Jess. Dean could tell that Sam hadn't invited her back to the suite, and that was fine with him. It was probably smart of Sam to hold off on subjecting her to the full frontal attack of Winchester/Singer nightlife. But that didn't mean he was enjoying saying goodnight either. The two stood awkwardly, pawing at each other very gently and making quiet, unfunny jokes in an effort to draw the evening out as long as possible. Dean's eyes arched over a familiar rainbow and found Cas's at the end of it.

_Time to go? _He raised an eyebrow at Cas.

_Let's blow this popsicle stand. _

Dean wasn't sure how Cas could embed proper nouns like _popsicle _so definitely into a look, but it made him laugh.

They retreated to the lobby where Jo hopped behind the counter to grab their room key. That plus the bottle of high-class gin was making her a very handy, if not unorthodox concierge. Cas nudged Dean and gestured towards Becky and Garth who were having an animated discussion on one of the benches by the door. Well Becky was conversing. Garth was watching with a strange mixture of fear and grateful amusement.

A few moments later Jess breezed past them all with a shy wave. Becky stopped gesturing and a watched her go, eyes darting back to Cas and Dean. Cas dipped his head and pointed after Jess. Becky nodded, hopped up, grabbed Garth's hand, shook it emphatically, then followed Jess out the door.

Jo called from somewhere behind them, holding an elevator.

"You don't think..." Dean started, remembering the gun in Becky's purse.

"No, Dean. Becky is not going to shoot Jess." Dean raised his eyebrows at Cas's deadpan. It wasn't an entirely implausible question. "Trust me."

And despite only knowing him for 48 or so hours, Dean did.


	6. Chapter 6

**A/N: _This is very revealing chapter, personally. Apparently if I were in charge of romance it would consist entirely of eating, dancing, and slumber parties. I swear there will be branching out to come. Back to the big store and then to Sam's show. Promise. I love your reviews - thank you Angela :)_**

**_..._**

Uncle Bobby Singer may have been a gruff dinner companion, but he was always generous. Their suite was located on the top floor, and consisted of a two full beds, a spacious bath, a plush couch and a breakfast table for four. Their luggage had been ferried up earlier by Garth, so they fell into the room empty handed, shucking off jackets and ties and throwing them haphazardly around the room, each claiming a corner or a space behind the couch for themselves without making it to a closet or a dresser like a civilized person. It was only one night.

Jo brought up the rear. She deposited the bottle of gin then disappeared back into the hall. Gabriel noticed her absence first, and walked right over the couch trying to get to the door and go after her. But when he reached the open door he was hit with a wall of cot. It toppled onto him with Jo behind it. She yelled upon impact, but was reduced to giggles as she rolled off of Gabriel and the temporary bed. Sam picked the cot up off of Gabriel and set it up near the couch. Gabriel dusted his hands at a job well done. Jo disappeared out the door once again.

After losing his coat and tuning in a raucous swing tune on the large radio, Dean moved on to pouring generous amounts of gin into the juice glasses already set up on the breakfast table.

"I had a feeling it was smart to keep the paying guests off this floor tonight."

Bobby appeared in the doorway with narrowed eyes. Sam swiped his hand through his hair nervously and Castiel straightened up and attempted to look responsible, though his tie hung loosely around his neck and his shirt sleeves were rolled to his elbows. Bobby's eyes darted around the room.

"Where's Jo?"

"Dropping off the gin was the last I saw of her." Dean answered innocently.

"Then what's that cot doing there?"

"I don't see it doing anything." Castiel blinked at Bobby, earnestly. Bobby's gaze remained cool. He was not as familiar with Castiel as he was with his nephews, but he was a quick study.

"I think I might just have to check and see if you boys have enough towels."

Bobby strode over to the bathroom. Jo immediately fell into the room with another cot. Sam's eyes went wide as he lunged forward to catch it before it made a thunk. He placed it gingerly next to the other cot while Gabriel gestured wildly to indicate to Jo that her father was in the bathroom. Luckily, Jo was good at charades. She tucked and rolled back out the door of the suite and made herself scarce in the hallway. Bobby walked out of the bathroom looking a bit more sour. He was under strict orders from Ellen to rope Jo in for the night and she wasn't making it easy. He saw the second cot and frowned.

"Why do you now have two cots?" He looked accusingly at Dean, which was silly. Dean hadn't moved an inch, and he gestured as much.

"Well you know how those things are. They multiply like rabbits." Castiel shrugged at him, a small smirk playing on his lips. Sam coughed out a laugh. Bobby barely stifled a grin with the knowledge that his wife would be none too happy with his next statement.

"Well do your best to keep Jo under control and out of her mom's hair for the night. I've managed to keep a whole two floors empty, aside from the regulars. But you're out as soon as I get a complaint, y'hear? Don't be idgits."

He directed his last order to Castiel, acting as if his being the eldest would somehow give him the ability to keep the group under control. Castiel wondered what kind of night he was in for. Bobby said a gruff goodnight and exited the room, closing the door behind him. It opened again 30 seconds later to reveal Jo triumphantly clutching a second bottle of liquor. She plunked it down next to the first.

"Now, who's hungry?"

…...

Castiel surprised everyone by volunteering to raid the Roadhouse kitchen with Jo. They were all hungry, and four hands were better than two. She led him down an employee staircase that wound them through a maze of staff tunnels and back entrances that were all very fascinating for someone not in the hospitality business. She brazenly snapped on the lights when they reached the long-closed kitchen, and gestured grandly.

"Tonight, we feast."

"Anything?"

"Anything." With that, she dove into a shallow cooler that was stocked with cheese platters, pre-prepared for room service. Castiel meandered over to the dessert case, snagging a full apple pie and a small tray of cream puffs.

Jo was busy piling her bounty onto a tray. She squinched her forehead when she saw Castiel's first picks.

"Dean likes pie," Cas explained, "and Gabriel thrives on any sort of sweet." He paused, considering whether there was enough food on the tray. "What does Sam eat?"

"Aren't you supposed to be the detective?"

"Tonight was the first meal I've shared with Sam, and I was hired to protect him more than detect him. My questions and observations are purely for the sake of curiosity."

"Hmm. Well Sam likes rabbit food, and Dean likes burgers and pie, though somehow you already seem to know all about Dean." She gave him a pointed look, but he did not meet her gaze.

Joe turned her back to Castiel to examine a different cooler. It was packed with raw meat, so she shut it abruptly. Castiel cleared his throat.

"I actually know very little about Dean. Is there anything that you could tell me that you think would be helpful - while I'm protecting Sam?"

Jo spun around thoughtfully. She searched Castiel's face for some indication of how much she should share about her favorite cousin. Castiel could see that she was assessing him in some way.

"Are you married?" She asked with some hesitation.

"No."

"Have you ever been engaged?"

"No."

"Just haven't met the right girl?"

"That's what I tell people." Cas began to look vaguely uncomfortable.

She bit her lip, and he could see her brain at work, the end result appearing to indicate that his perpetual bachelorhood had somehow earned her trust.

"Well from what I heard Dean was a lot crazier during the speak-easy days, when his dad was still alive and Sam was over in Europe for music school. Right at the end of prohibition there were a lot of raids at some of the big spots downtown, and he got picked up more than once. No one will tell me exactly what for..."

Castiel's eyebrows shot up. He knew who had been raided and why. He'd even witnessed one such event while tailing a man who was suspected of stepping out on his wife. The raid itself had usurped his commission, when the cops picked up his mark and charged the man with public indecency. The man's wife had not felt inclined to deliver the final payment after suffering the public humiliation that comes with your husband being arrested in a stunning ball gown.

"I see." Castiel's answered gravely.

"Yeah, I think you might." Jo looked at him for a few seconds more, straining to interpret every facet of his reaction. For the second time that evening he admired her keen ability to pry.

"Well, the only greens I've encountered seem to be garnish, and I don't think there's enough parsley in the whole state of Illinois to fill Sam Winchester." Castiel worried loudly to break the tension.

Jo laughed and dug around in a different cooler. She found some carrot sticks and held them up, triumphantly.

"There. Rabbit food."

They finished loading their tray and Jo surprised Castiel yet again by hoisting it up onto her shoulder like a pro. He attempted to help, but she waved him away with a mystifyingly free hand. She only had to transport their food across the kitchen to the dumbwaiter attached to their suite, and send it up to the top floor. The pair took the stairs two at a time, back to the suite and the feast that now awaited them. They burst through the door with hunger in their eyes. Their friends had not felt the need to wait for their arrival.

"Good call on the pie, Cas!"

Cas smiled back, though his eyes flickered momentarily as he watched Dean eat the uncut pastry directly out of the pie plate.

"You're welcome, though I was looking forward to trying a piece."

Dean tossed him a fork.

Gabriel was making short work of a platter of assorted cheeses, with the help of a long loaf of French bread. Jo joined him.

Sam hovered overhead, picking at the cheese and assorted meats until his eyes lit up. He had found the carrots. His crunching filled the room, and no one hesitated to roll their eyes at him.

No matter what they were eating, they were washing it down with gin, and it wasn't long before they all felt rather loose, if a bit drowsy. An upbeat hit came on the radio, and Gabriel jumped up and tried to pull Jo off the couch to dance. She groaned and refused to budge. Gabriel shrugged and grabbed Castiel, who made noises of protest, but allowed himself to be pulled to his feet. His cousin took the lead and whirled him around. Castiel played along, and followed a bit goofily.

"Sam. Sam. Sam." Jo picked herself up and started poking Sam in his side. "We can't let them show us up like this."

"Save yourself the embarrassment." Castiel called out. "I'm the best dancer in this room." Gabriel gave him a _says you_ glare, and looked to the others for support.

Those were the magic words. Before Sam knew what hit him he was being jerked around the room by his petite cousin. Their size difference made them seem a bit graceless, but they held their own for a minute or two. Sam was coordinated, and had good rhythm, while Jo was blessed with the absence of fear. Dean sat back and laughed at Jo's face, screwed up with competitive concentration.

The song ended abruptly, and the DJ came on to announce the next track, a hit entitled "Your Face" by the up and coming Sam Winchester. The pace slowed down a tad, though the tempo of his song was still upbeat. Everyone but Sam (and Gabriel, technically, though he mimicked the action) yelled out when they heard his name. Sam groaned and sat himself back on the couch, covering his face with his hands. He would never be used to listening to his songs in front of the people that were close to him. It felt a bit too personal and left him wide-open for some brotherly ribbing.

Castiel abandoned Gabriel in favor of Jo, and began to waltz her around the room.

"Still the best dancer in the room." He threw it out to take some of the heat off Sam. It seemed to work. Jo bristled and complained that she couldn't compete fairly if she had to follow his lead. She took the opportunity of a tight turn to push away. He thudded into the table next to Dean and snatched up Dean's hand before the man could protest. Jo had snatched Gabriel up again. Dean balked a moment.

"Where's your competitive spirit, Deano?" Singer yelled out, swiveling her hips to the beat. Dean narrowed his eyes, the full effect of his drinking swimming up to his brain and exploding with intent.

"You lead." He commanded. "I refuse to be beaten while dancing to my own brother's song."

Castiel took Dean's firm waist in his arm while Dean circled his shoulder. They joined hands. Cas straightened and Dean mirrored the motion, which brought them few inches closer together. They could smell a spicy mix of gin and apple pie mingling between them.

"Are you ready to judge this competition, Sam? Castiel waited for a downbeat before leading his partner out onto the"floor."

"Sure. What's the prize?"

"The coveted title of best dancer." Castiel spoke earnestly.

"And moooore gin!" Called Jo.

"Step it up, Cas. I could always use more gin."

Cas pulled Dean around the room like an expert, though Dean held his own and completed some pretty tricky steps considering the backwards nature of his side of the action. Castiel was a strong lead. By the end of the song they were the clear winner, Gabriel having tried to leap over a coffee table and failed, accidentally throwing Jo into Sam, landing them both in a heap on the couch.

"Oof," gasped Sam. "You lose. Castiel is easily the best dancer in the room and surprisingly Dean didn't do so bad either."

Dean whooped and Cas smiled knowingly. Jo began to pout. Gabriel took pity on her and offered her a cream puff from his pocket. She accepted her consolation prize with only a little grace.

Once the mystery of the greatest dancer was solved, the party began to wind down. Sam pulled his bag into the bathroom and emerged shirtless in his where's-the-flood pajama bottoms. Dean pointed at him with bleary eyes in a way that said _I am laughing at you, Moose._ Sam rolled his eyes and collapsed on one of the plush hotel beds.

Jo had spent the last hour curled up in the corner of the couch, talking at Gabe. He had done a lot of absent nodding, and occasionally elicited a squeal of delight when he pulled colorful scarves from her ear or surprised her by honking his little bicycle horn in response to a question. She nodded off just after Sam went to sleep. Gabriel smiled and stood. He surveyed her critically and did a few squats, apparently trying to loosen up a bit. He mimed spitting into each palm, then rubbed his hands together. Then, ever so gently, he slid his arms around the sleeping girl and hoisted her off the couch. He paused for a moment, but she didn't stir, so he gingerly walked them across the room and deposited her onto the other hotel bed.

Dean and Cas were heavily buzzed, and were handling their guilt about that in different ways. Dean would pace the room, periodically peering out the windows to "make sure nothing was up," while Cas would take leave of the suite every half hour to "clear the hall." Neither one of them had seen anything remotely suspicious, but that didn't stop them from giving everything a wary eye, including the two cots that Gabriel left for them after snuggling his fluffy head into the warm spot Jo left in the corner of the couch.

"Should we do this in shifts?" Dean asked Cas, only slurring a little.

"We both need to sleep, Dean. It'll be fine." Cas's paranoia was slightly dimmed by the fact that Sam was not his flesh and blood brother. But also because he was more and more considering Dean to be part of his responsibility as well, and after their night on the street, Dean needed a real sleep. He pushed Dean over to the outside cot, and climbed onto the middle one himself. Dean stared at nothing while he loosened his tie and untucked his shirt. He flicked the last light switch in the room off then settled himself onto the narrow bed.

Castiel was only 8 or so inches away from both Gabriel and Dean, the group having never re-arranged after Jo's hurried bed deliveries. Gabriel let out a snort, and Dean reached over to hit him with a pillow, effectively smashing Cas across the shoulder. Castiel kicked Dean in the shin, and Dean growled. A moment later he laughed quietly.

"How'd I get roped into another night with you two clowns?" He asked no one in particular.

"Better than sleeping in your Chevy." Cas pointed out, logically.

"Nothing is better than my baby," Dean grumbled.

Cas turned his head to face Dean for a moment through the dark, and Dean could feel him huff out a chuckle, and practically heard him rolling his eyes.


End file.
